Taste-modified creatine salts, compounds, compositions and uses thereof

Abstract

Provided are embodiments of creatine and creatine ethyl ester (CEE) salts where the anion is an artificial (non-saccharide) taste-modifier. These compounds represent stable white non-hygroscopic solids or semisolids that can readily dissolve in water and buffer solutions. Synthesis of novel creatine salts using environmentally safe solvents such as ethanol resulted in the formation of products in quantitative yields with sodium or potassium chloride as a byproduct. The creatine and creatine alkyl eater derivative salts are stable sweet-tasting compounds that are more palatable to a consumer than creatine or derivatives thereof.

We claim: 
     
       1. A creatine salt or a solvate thereof, comprising creatine or a cationic derivative of creatine and an anionic taste-modifier, the creatine salt having formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  and R 2  are each independently a hydrogen or an alkyl group; 
         R 3  is H or an alkyl group; and 
         X is selected from the group consisting of saccharinate, acesulfamate, neotamate, cyclamate, and steviolate. 
       
     
     
       2. The salt of  claim 1 , wherein cationic derivative of creatine is a creatine alkyl ester cation. 
     
     
       3. The salt of  claim 1 , wherein R 3  is an alkyl group. 
     
     
       4. The salt of  claim 1 , wherein R 3  is selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, and a palmitoleate group. 
     
     
       5. The salt of  claim 1 , wherein the creatine alkyl ester cation is a creatine ethyl ester (CEE) cation. 
     
     
       6. The salt of  claim 1 , wherein the anionic taste-modifier is selected from the group consisting of saccharinate and acesulfamate. 
     
     
       7. The salt of  claim 1 , wherein said salt is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
       8. A composition comprising at least one creatine salt or solvate thereof, wherein each of the at least one creatine salt or solvate thereof comprises creatine or a cationic derivative of creatine and an anionic taste-modifier, the creatine salt having formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  and R 2  are each independently a hydrogen or an alkyl group; 
         R 3  is H or an alkyl group; and 
         X is selected from the group consisting of saccharinate, acesulfamate, neotamate, cyclamate, and steviolate. 
       
     
     
       9. The composition of  claim 8 , wherein the cationic derivative of creatine is a creatine alkyl ester cation. 
     
     
       10. The composition of  claim 8 , wherein R 3  can be an alkyl group. 
     
     
       11. The composition of  claim 10 , wherein R 3  is selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, and a palmitoleate group. 
     
     
       12. The composition of  claim 9 , wherein the creatine alkyl ester cation is a creatine ethyl ester (CEE) cation. 
     
     
       13. The composition of  claim 8 , wherein the anionic taste-modifier is selected from the group consisting of saccharinate and acesulfamate. 
     
     
       14. The composition of  claim 8 , wherein each of the at least one of said salts is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
       15. The composition of  claim 8 , wherein said composition is a powder, a non-aqueous oil, or a semi-solid. 
     
     
       16. The composition of  claim 8 , further comprising an aqueous medium in an amount that does not result in dissociation of the creatine or a cationic derivative of creatine, and the anionic taste-modifier. 
     
     
       17. The composition of  claim 16 , wherein the percent weight of the aqueous medium is from 0.001% to about 30%, from 0.001% to about 20%, 0.001% to about 10%, from 0.001% to about 5%, from 0.001% to about 2%, from 0.001% to about 1%, from 0.001% to about 0.5%, or from 0.001% to about 0.1%. 
     
     
       18. The composition of  claim 8 , wherein the creatine or cationic derivative of creatine, and the anionic taste-modifier are admixed with a non-aqueous medium. 
     
     
       19. The composition of  claim 18 , wherein the non-aqueous medium is an edible oil or lipid. 
     
     
       20. The composition of  claim 8 , wherein the composition is in a foodstuff or beverage formulated for consumption by a human or animal. 
     
     
       21. A dietary supplement composition contained in a bulk package,
 wherein the dietary supplement composition is a powder, a non-aqueous oil, or a semi-solid, 
 optionally wherein the bulk package further comprises a measuring scoop sized to scoop an amount of the dietary supplement composition suitable for blending with a liquid to form a single serving of a beverage, 
 wherein the dietary supplement composition consisting essentially of at least one creatine salt or solvate thereof of  claim 1 . 
 
     
     
       22. The dietary supplement composition contained in the bulk package of  claim 21 , wherein the cationic derivative of creatine is a creatine alkyl ester cation. 
     
     
       23. The dietary supplement composition contained in the bulk package of  claim 22 , wherein the creatine alkyl ester cation is a creatine ethyl ester (CEE) cation. 
     
     
       24. The dietary supplement composition contained in the bulk package of  claim 21 , wherein the anionic taste-modifier is selected from the group consisting of saccharinate and acesulfamate. 
     
     
       25. The dietary supplement composition contained in the bulk package of  claim 21 , wherein each of the at least one said salts is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
       26. The salt of  claim 1 , wherein said salt is 
       
         
           
           
               
               
           
         
       
     
     
       27. A creatine salt or a solvate thereof, comprising creatine or a cationic derivative of creatine and an anionic taste-modifier, the creatine salt having formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  and R 2  are each independently a hydrogen, an alkyl group, or a hetaryl group; 
         R 3  is H or an alkyl group; 
         X is taurocholate; and 
         wherein the creatine salt has a reduced bitter taste compared to creatine. 
       
     
     
       28. The salt of  claim 27 , wherein said salt is selected from the group consisting of: